KR100271070B1 - Permanent waving with silicones - Google Patents

Abstract

The present invention relates to a method for reducing the cystine bond to cysteine, forming a wave in the hair and counteracting the hair to perm the hair, wherein the reverse reaction step is carried out by applying to the hair a composition comprising a vinyl functional silicone, an oxidizing agent such as hydrogen peroxide and a carrier fluid. It relates to a perm method of hair and a neutralizer composition for hair perm characterized by performing.

Description

[Name of invention]

Neutralizer composition for hair perm

Detailed description of the invention

The present invention relates to a method of permanent waving hair and silicone-based neutralizing agent compositions useful for hair perming.

Keratin is a fibrous protein consisting of 18 different amino acids. It is widely distributed in hair and is the main constituent of hair. Keratin is characterized by a crosslinking structure with one disulfide bond (-SS-) per 10-20 amino acid residues on average. Keratin is mainly represented by the cystine of the structural formula HO ₂ CC (NH ₂ ) HCH ₂ S-SCH ₂ C (NH ₂ ) HCO ₂ H.

The first basic step in hair permation is partially cystine [HO ₂ CC (NH ₂ ) HCH ₂ S-SCH ₂ C (NH ₂ ) HCO ₂ H] to cysteine [HO ₂ CC (NH ₂ ) HCH ₂ SH]. To reduce. Generally, wave lotion containing thioglycolic acid is used in the reaction step in which the cystine bond is reduced to cysteine. After wave formation on the hair, the reaction is reversed by applying a neutralizer, a solution containing an oxidizing agent such as hydrogen peroxide, to the hair. Cysteine residues formed during the reduction step are converted back to cystine during neutralization.

There is a need in the art for more effective perm neutralizer compositions. The present invention is to perm the perm neutralizer composition in the form of a silicone based composition which has been found to work effectively as a keratin crosslinker with an oxidant such as hydrogen peroxide in the perm of hair. Silicone is believed to be part of the covalent crosslinker between the keratin fibers of the hair, providing a wave. In addition, the use of silicone-based compositions gives silicones additional benefits to hair such as conditioning, providing flexibility and softness to hair and enhanced ease of combing.

The present invention relates to a hair perm method and a composition therefor. In particular, a silicon-based neutralizing agent is used to reform the cystine structure from the cysteine residues generated during the reduction step of the perm process. The neutralizing agent composition of the present invention comprises vinyl functional silicone, tetracycline such as hydrogen peroxide, and a suitable carrier fluid for dispensing the active ingredient.

When used in combination with a hydrogen peroxide neutralizing agent solution, the composition of the present invention has the advantage of simultaneously providing a conditioning effect to the hair and simultaneously acting as a keratin crosslinking agent.

In addition to vinyl functional silicone oxidants and suitable carrier fluids, the neutralizing agent compositions of the present invention may further include humectants and foaming agents to increase dispersion and retention of the composition on the hair, increase flexibility, facilitate combing, and Other conditioning agents may be included to control blowing.

Both cyclic and linear vinyl functional silicones can be used. Suitable vinyl functional silicones that may be considered can be represented by the following general formula.

(Ⅰ)

(II) Me ₃ SiO (MeViSiO) _x (RR'SiO) _y (R "R"'SiO) _z SiMe ₃

(III) Me ₃ SiO (MeViSiO) _x (R "R"'SiO) _z SiMe ₃

(IV) Me ₃ SiO (MeViSiO) _x (RR'SiO) _y SiMe ₃

(V) Me ₃ ViSiO (MeViSiO) _x (RR'SiO) _y (R "R"'SiO) _z SiMe ₃ Vi

(VI) Me ₃ ViSiO (RR'SiO) _y (R "R"'SiO) _z SiMe ₃ Vi

(Ⅶ) Me ₃ ViSiO (MeViSiO) _x (R "R"'SiO) _z SiMe ₃ Vi

(Ⅷ) Me ₃ ViSiO (MeViSiO) _x (RR'SiO) _y SiMe ₃ Vi

Wherein n is an integer from 3 to 30, preferably 5, and R, R 'R "and R"' are each an alkyl group or phenyl having 1 to 5 carbon atoms, preferably each is methyl,

Me is methyl,

Vi is CH ₂ = CH-,

x, y and z are each from 1 to 1000.

General formula (I) represents cyclic vinyl functional silicone, and general formulas (II) to (IX) represent linear materials. Such vinyl functional silicones and their preparation are known in the art. All compounds are commercially available.

The silicone compounds of general formulas (I) to (IX) serve in accordance with the concept of the present invention, but particularly preferred vinyl functional silicones are those which have a low polymerization copper (DP) and a high vinyl functional group. Representative vinyl functional silicones are as follows, and Me, Vi, and x have the meanings described above.

(Ⅸ) Me ₂ ViSiO (MeViSiO) _x SiMe ₂ Vi

(Ⅹ) Me ₂ ViSiOSiMe ₂ Vi

(ⅩⅠ)

In general formula (VII) and (XI), x is 1-1000. In general formula (x), x is preferably 1 50, and in general formula (xI), x is preferably 10 to 1000, most preferably 10 to 100.

The compound of formula IV is divinyltetramethyldisiloxane, and this vinyl functional disiloxane can be used in the form of a mechanical emulsion containing 35% by weight of disiloxane. In the examples and tables below, the disiloxane "silicone 1" of the general formula (VII) and the mechanical emulsion of the disiloxane are referred to as "silicone 2". Formula (XI) is an emulsion polymer prepared by emulsion polymerization of cyclic methylvinylsiloxane. In the examples and tables below, this emulsion polymer is referred to as "silicone 3". Formula (VIII) is another polymer prepared by emulsion polymerization of divinyltetramethyldisiloxane and cyclic methylvinylsiloxane, and is represented as "silicone 4" in the following Examples and Tables. Particular polymers used as "silicone 4" have a DP of 10.

Methods of preparing mechanical emulsions and of preparing emulsions using emulsion polymerization are well known in the art. All standard methods for preparing the above-mentioned mechanical emulsions and emulsion polymers can be used. See, for example, methods for preparing mechanical emulsions-European Patent Application No. 0460683A2. Release date: 11/11/1991; Process for preparing emulsion polymer-European Patent Application No. 0459500A2. Date of publication December 4, 1991].

Mechanical emulsions are prepared by mixing silicone with one or more surfactants in water. Anionic, nonionic and cationic surfactants can be used to stabilize the emulsion. To improve the stability, it is often advantageous to use mixtures of two or more surfactants, for example two nonionic surfactants, anionic and nonionic surfactants or mixtures of cationic and nonionic surfactants. Typically, 1 to 30 parts by weight of surfactant is used per 100 parts by weight of silicone.

In emulsion polymerization, reactive silicone oligomers, surfactants, polymerization catalysts and water are mixed. The mixture is stirred and the oligomer is polymerized until an emulsion is formed. Typically, alkoxysilanes or cyclic siloxanes are used as reactive monomers and oligomers. Mixtures of silicone reactants may be used to form copolymers in the product emulsions.

It is believed that the crosslinking of the hair with vinyl functional silicone takes place according to the mechanism shown below, where cyclic vinyl functional silicone is used for illustrative purposes.

In the scheme, K is HO ₂ CC (NH ₂ ) HCH ₂ -or a polymeric derivative thereof.

As the carrier fluid, alcohols, hydrocarbons, halogenated hydrocarbons, water, mixtures of alcohol and water or volatile silicones can be used. Representative carrier fluids are ethanol, isopropyl alcohol, inorganic spirits, trichloroethane and dichlorotetrafluoroethane.

If it is desired to use a silicone carrier fluid, the volatile silicones according to the invention are low viscosity methylsilicone fluids. The volatile low viscosity methylsilicone fluid corresponds to the average unit of the general formula (CH ₃ ) _a SiO _{(4-a) 2} , where a is an integer having an average value of 1 to 3. Methylsilicon fluids are siloxane units bound by Si-O-Si bonds. Representative units are (CH ₃ ) ₃ SiO _1/2 , (CH ₃ ) ₂ SiO _2/2 , (CH ₃ ) SiO _3/2 and SiO _4/2 . These units are present in molar amounts providing an average of 2 to 3 methyl groups per silicon atom in the methylsilicone fluid, where the methylsilicone fluid has a viscosity measured at 25 ° C. of less than 100 mm 2 / s (centistog).

Volatile low viscosity methylsilicone fluids contain dimethylsiloxane units and optionally trimethylsiloxane units. Preferably the methyl silicone fluid has a viscosity of 10 mm 2 / s or less (centistokes) or less. Representative compounds include cyclopolysiloxane compounds of the general formula [(CH ₃ ) ₂ SiO] x and linear siloxane compounds of the general formula (CH ₃ ) ₃ SiO [(CH ₃ ) ₂ SiO] _y Si (CH ₃ ) ₃ ( Where x is an integer of 3 to 10 and y is an integer of 0 to 4).

Volatile low viscosity methylsilicon has a boiling point of generally 250 ° C. or less and a viscosity of 25 ° C. or less, 10 mm 2 / s (centistokes) or less, most preferably 0.65 to 5.0 mm 2 / s (centistokes). Cyclopolysiloxane compounds are commercially available under the trademark "CYCLOMETHICONE" (Cosmetics, Toiletries and Fragrance Association, Inc., Washington, D.C. (CTFA)). Both cyclopolysiloxanes and linear siloxanes are clear fluids and are almost odorless, non-toxic, non-oil and non-irritating. In cosmetics these methylsilicone fluids are not irritating to the skin, are well developed and easy to remove when applied. Once applied, the material evaporates without residue.

Methylsilicone applicable according to the present invention is substantially free of residue after 30 minutes at room temperature when 1 g of fluid is placed in the center of No. 1 circular filter paper having a diameter of 185 mm and its periphery maintained at room temperature atmosphere. Methylsilicone fluid means a composition containing two or more silicon atoms, in which one or more oxygen atoms are bonded to one or more other silicon and one or more methyl radicals, wherein each silicon valence not satisfied by oxygen is represented by a methyl radical Are satisfied.

Representative methyl silicone fluids identified as particularly useful in accordance with the present invention include octamethyltrisiloxane, having a hexamethyldisiloxane acid boiling point of 99.5 ° C., a Me ₃ SiOSiM ₃ boiling point of 152 ° C., and a Me ₃ SiOMe ₂ SiOSiMe ₃ structure; Hexamethylcyclotrisiloxane, having a boiling point of 133 ° C. and a structural formula of [(Me ₃ ) SiO] ₃ ; Octamethylcyclotetraoxane having a boiling point of 171 ° C. and a structural formula of [(Me ₂ ) SiO] ₄ ; And decamethylcyclopentasiloxane, having a boiling point of 205 ° C. and a structural formula of [(Me ₂ ) SiO] ₅ .

Such methylsilicone fluids may be used alone or as a mixture of two or more. Mixtures of methylsilicone fluids are volatiles that differ in evaporation behavior from individual methylsilicone fluids. Methylsilicone fluids and their preparation are known in the art and commercially available.

In some instances, it may be desirable to substitute one or more methyl groups with other groups in the methylsilicone fluid. Thus, alkyl radicals having 2 to 12 carbon atoms; Aryl radicals having 6 to 10 carbon atoms; Amine groups; vinyl; Hydroxyl; Haloalkyl group; Aralkyl group; And groups such as acrylate groups.

The composition of the present invention is suitable for use in a perm weaving method such as a hot wave process, a mild wave method and a cold wave method. For example, in a typical cold wave method, the hair is first shampooed, the newly shampooed hair is divided into 40 to 60 bundles. Each bundle is moistened with a wave lotion and put in a plastic curler. The size of the color determines the characteristics of the wave generated. For example, small colors have a dense wave. The hair is washed thoroughly and neutralized with a neutralizer solution. The hair is then loosened, washed again and dried or set in the desired style.

The composition according to the invention contains 0.1 to 10% by weight of vinyl functional silicone, 0.1 to 5.0% by weight of an oxidizing agent such as hydrogen peroxide and 85.0 to 99.8% by weight of the carrier fluid. The following examples are intended to illustrate the invention in more detail.

Example I

2.4 g of dark brown virgin European hair, 20.3 cm (8 inches) long, is glued to a 2 inch square plastic tab to form a hair bundle. After the glue has cured, each hair is cut to 15.2 cm (6 in) in length. The bundle is washed with tap water at 40 ° C., 0.5 ml of sodium lauryl sulfate-based shampoo is applied for 30 seconds, and the hair is washed and shampooed for 30 seconds.

Example II

Tighten and comb the bundle of hairs to the vent. 1 g of perm wave reduction solution is applied to each bundle and the hair is combed. The hair is curled onto the perm weaving rods using standard perm waving and paper and an additional 1 g of the perm wave reducing solution is applied to the hair using a syringe. Hold the rolled hair for 15 minutes. To resemble human hair conditions, ten thousand hair bundles are placed in plastic bags and placed in a 40 ° C. oven for 10 minutes.

Example III

Only remove the bundle of hair from the oven and rinse with warm tap water for 1 minute. The hair is absorbed with a paper towel and dried. Each hair is placed in a weighing dish and 1.5 g of neutralizer solution is applied by syringe. In addition 2 g of neutralizing agent are added to the weighing dish. After 5 minutes, the bundle is released from the rod and excess neutralizer is removed from the bundle and placed back into the weighing dish. The hair bundle is rinsed with tap water for 1 minute and hanged at room temperature to dry.

Example IV

After 2 days, the bundle for evaluation is prepared. Both sides of each hair are labeled "left" and "right" and the bundle is cut in half lengths. The “right” half is washed with 40 ° C. tap water and shampooed by applying 0.25 ml of blank shampoo and washing the bundle for 15 seconds. Repeat the shampooing four times in a bundle of "right" half and dry. The bundle of "right" halves is evaluated by comparison with the bundle of "left" halves that have not been cleaned.

The evaluation is performed using the procedure of Examples I to IV described above. Use of the perm waving kits (including those containing thioglycolic acid and those containing glyceryl monothioglycolate) available commercially as "comparative". Commercially available neutralizing agent solutions are used in the oxidation step, respectively. As another "comparative" use a solution containing 7.6% by weight of thioglycolic acid in water and the pH of the other comparative solution is adjusted to 9.5 using ammonium hydroxide. Another "comparative solution" is shown as "THIO BLANK" in the table below. The "thioblank" is neutralized with a 2% solution of hydrogen peroxide in water and adjusted to pH 3.4-3.7 with phosphoric acid.

The compositions of the present invention are evaluated for comparative compositions in three different ways. In "Method A", 2% vinyl functional silicone is added to the perm reducing solution. In "Method B" 2% of vinyl functional silicone in water or in a mixture of water and alcohol is applied as an intermediate step between the reduction and neutralization steps. In "Method C", 2% vinyl functional silicone is added to the neutralization solution.

The permed hair bundles prepared according to Examples I-IV are evaluated after cutting the "right" half shampooed as in Example IV. Uncleaned “left” and cleaned “right” halves are evaluated under sensory criteria by grading the number of curls, ease of combing, and soft feel. Grades 1 to 5 are used, with 1 representing the best and 5 representing the lowest. Evaluated by the person performing the process. Tabulate incremental differences of 0.25 units. The evaluation results are shown in Tables I and II.

Table I shows improvement over the comparables in all ranges of sensory tests. Best results are obtained with "thio blanks". Table II compares the compositions of the invention with the comparative for deterioration of curl, combability and feel after 5 shampoos. It is clear that the degradation is much reduced when using "thio blanks".

TABLE I

TABLE I (CONTINUED)

TABLE II

Table II (continued)

The composition of the present invention may contain other components in addition to the vinyl functional silicone, oxidant and carrier fluid. For example, auxiliaries customary in perm and neutralizer compositions can be used as components. For example, auxiliaries which may be included are reducing agents, coloring agents, perfume oils, opacifying agents, surfactants, emulsifiers and cationic resins.

Claims (5)

A neutralizer composition for hair perm comprising 0.1 to 10.0% by weight of vinyl functional silicone of the following general formula, 0.1 to 5.0% by weight of oxidizing agent and 85.0 to 99.8% by weight of carrier fluid. Me ₂ ViSiO (MeViSiO) _x SiMe ₂ Vi Me ₂ ViSiOSiMe ₂ Vi In the above formula, Me is a methyl radical (-CH ₃ ), Vi is a vinyl radical (CH ₂ = CH-), x is an integer from 1 to 1,000. The composition of claim 1 wherein the carrier fluid is selected from alcohols, hydrocarbons, halogenated hydrocarbons, volatile silicones, water and mixtures of water and alcohols. The composition of claim 1 wherein the oxidant is hydrogen peroxide. The composition of claim 1 wherein the vinyl functional silicone is in the form of an emulsion prepared by mechanical emulsion or emulsion polymerization. The composition of claim 1 wherein x is from 1 to 50.